183948-71-2Relevant academic research and scientific papers
Biosynthesis of jasmonic acid in a plant pathogenic fungus, Lasiodiplodia theobromae
Tsukada, Kohei,Takahashi, Kosaku,Nabeta, Kensuke
, p. 2019 - 2023 (2010)
Jasmonic acid (JA) is a plant hormone that plays an important role in a wide variety of plant physiological processes. The plant pathogenic fungus, Lasiodiplodia theobromae also produces JA; however, its biosynthesis in this fungus has yet to be explored. Administration of [1-13C] and [2- 13C] NaOAc into L. theobromae established that JA in this fungus originates from a fatty acid synthetic pathway. The methyl ester of 12-oxo-phytodienoic acid (OPDA) was detected in the culture extracts of L. theobromae by GC-MS analysis. This finding indicates the presence of OPDA (a known intermediate of JA biosynthesis in plants) in L. theobromae. 2H NMR spectroscopic data of JA produced by L. theobromae with the incorporation of [9,10,12,13,15,16-2H6] linolenic acid showed that five deuterium atoms remained intact. In plants, this is speculated to arise from JA being produced by the octadecanoid pathway. However, the observed stereoselectivity of the cyclopentenone olefin reduction in L. theobromae was opposite to that observed in plants. These data suggest that JA biosynthesis in L. theobromae is similar to that in plants, but differing in the facial selectivity of the enone reduction.
Preparation of (±)-2-(2,3-2H2) jasmonic acid and its methyl ester, methyl (±)-2-(2,3-2H2)jasmonate
Seto,Fujioka,Fujisawa,Goto,Nojiri,Yamane,Yoshida
, p. 1709 - 1711 (2007/10/03)
For use as the internal standards in a quantitative analysis of natural jasmonic acid (JA) and methyl jasmonate (JAMe) by gas chromatography-mass spectrometry-selected ion monitoring, (±)-2-(2,3-2H2)JA and its methyl ester, (±)-2-(2,3-2H2)JAMe, were efficiently prepared from 2-(2-pentyl)- 2-cyclopentenone through catalytic semi-deuteriogenation of acetylenic intermediates with deuterium gas in pyridine.
